The Agenda: 51st Annual Christmas Stroll on Nantucket
Holiday markets, Santa sightings, live music, and more.
From December 5 through 7, the cobblestoned streets of Nantucket are transformed into something of a Dickensian tableau during the island’s 51st Annual Christmas Stroll. Conceived in 1973 by a collective of savvy island merchants, the weekend event was originally founded to combat the pre-winter exodus, enticing islanders and mainlanders alike to stay, visit, and most importantly, shop locally. Today, this tradition draws thousands to support Nantucket’s cherished small businesses while enjoying the incomparable holiday ambiance of the historic district.
This year’s Stroll is chock-full of festivities—from shopping events and Santa sightings to live music and beyond—outlined below. Happy Strolling!
“It’s the one night of the year when we all act a little nicer, we smile a little easier, we cheer a little more. For a couple of hours out of the whole year we are the people that we always hoped we would be.”
— Frank Cross, Scrooged
Friday, December 5
Ease into the weekend with local markets, festive tours, and the first toast of the season.
9:00 AM: Wreath Making Workshop
Bartlett’s Farm (33 Bartlett Farm Road)
*Ed. Note: Other sessions start at 11:00 AM and 1:00 PM.
9:00 AM – 4:00 PM: Holiday Farmers & Artisans Market
Nantucket Yacht Club (1 South Beach Street)
*Ed. Note: Skip the generic gifts and head here first. It’s the perfect spot to grab local pottery, hand-knit goods, and island-made jewelry before the Saturday crowds descend.
10:00 AM – 4:00 PM: Whaling Museum Festival of Trees
Whaling Museum (13 Broad Street)
*Ed. Note: Opening day; runs through December. Dozens of locally designed trees set against the backdrop of the historic museum. It’s arguably the most Instagrammable spot of the weekend.
1:00 PM – 3:00 PM: Bubbles & Stroll Tasting
Épernay Wine & Spirits (1 N Beach Street)
4:00 PM – 7:00 PM: Holiday House Tour
Various Locations (Begins at 2 Centre Street)
*Ed. Note: A chance to step inside some of the island’s most stunning historic homes and churches, all dressed up for the holidays. Proceeds benefit Friends of Nantucket Public Schools.
5:00 PM - 6:30 PM: The Nantucket Ghost Walk
Various Locations (Begins at the corner of India and Federal Streets)
5:00 PM - 8:00 PM: Live Music on the Front Porch
The Nantucket Hotel (77 Easton Street)
*Ed. Note: Carolers, cocktails, and more.
7:00 PM - 8:00 PM: Christmas Concert
St. Paul’s Episcopal Church (20 Fair Street)
7:00 PM - 10:00 PM: 5th Annual Nantucket Dreamland Stroll Party
Dreamland Nantucket (17 S Water Street)
*Ed Note: A ticketed event with a DJ performance by the Hess Twins.
7:00 PM - 10:00 PM: Deck the Wharf Bash
Maria Mitchell Association at Straight Wharf Fish (4 Harbor Square)
Saturday, December 6
The big day. Wear your festive best (yes, that means ugly sweaters, reindeer antlers, flashing bulb necklaces—Stroll knows no style shame!).
9:00 AM – 4:00 PM: Holiday Farmers & Artisans Market
Nantucket Yacht Club (1 South Beach Street)
9:30 AM: Christmas Stroll Auction
Rafael Osona (21 Washington Street)
9:30 AM – 3:00 PM: Christmas Market
St. Paul’s Episcopal Church (20 Fair Street)
10:00 AM – 2:00 PM: St. Mary’s Cookout
St. Mary’s Church (3 Federal Street)
10:00 AM – 3:00 PM: 51st Annual Christmas Stroll Marketplace
Nantucket Island Chamber of Commerce at the Stop & Shop Downtown Lot (9 Salem Street)
*Ed. Note: This is what Stroll is all about. Support local businesses!
10:00 AM - 5:30 PM: Book Signings
Mitchell’s Book Corner (54 Main Street)
*Ed. Note: 10:00 AM - 11:00 AM with Alison Barone and Annabelle Meszynski, author and illustrator (respectively) of Nantucket Nelly and the Christmas Stroll; 11:00 AM - 12:00 PM with Leslie Linsley, author of Christmas on Nantucket; 12:00 PM - 1:00 PM with Pamela Kelley, author of Christmas at the Nantucket Restaurant; 1:00 PM - 2:00 PM with James Sulzer, author of All That Smolders; 2:00 PM - 3:00 PM with Nancy Thayer, author of Summer Light on Nantucket and A Very Nantucket Christmas; 3:00 PM - 4:00 PM with Nathaniel Philbrick, author of In The Heart of the Sea and Travels with George; 4:00 PM - 5:30 PM with Elin Hilderbrand, author of The Academy and Winter Street Series
10:00 AM – 1:00 PM: Holiday House Tour
Various Locations (Begins at 2 Centre Street)
10:00 AM – 4:00 PM: Yuletide Fair
Nantucket Lighthouse School at White Elephant Ballroom (19 N Water Street)
11:00 AM – 7:00 PM: Cisco Brewers
Cisco Brewers (Bartlett Farm Rd)
*Ed. Note: Take the shuttle from downtown. Live music, raw bar, and festive crowds.
12:00 PM (Sharp!): Santa’s Arrival by Boat
Straight Wharf
*Ed. Note: The Town Crier announces 10 minutes before the event. Santa arrives via Coast Guard cutter. Avoid the crowd at the dock; instead, watch from the gazebo area or stake out a spot on Main Street early to see him parade up to the Pacific National Bank.
1:30 PM – 2:30 PM: The Talking Tree
Main Street
*Ed. Note: Pure nostalgia. The “Talking Tree” is a quirky island tradition that terrifies and delights children in equal measure.
3:00 PM – 4:30 PM: Accidentals & Naturals
Main Street
*Ed. Note: Nantucket High School’s chorus performs a selection of holiday songs.
3:30 PM – 4:00 PM: Ugly Sweater Contest
Main Street
4:15 PM – 5:00 PM: Victorian Carolers Sing-Along
Main Street
Sunday, December 7
The cherry on top of a weekend full of holiday cheer.
7:00 AM: Monument Running Group Annual Winter Run
Various Locations (Begins at Nantucket Run Centre, 36 Centre Street)
1:00 PM – 4:00 PM: Ornament Making
Maria Mitchell Association at the Hinchman House Natural Science Museum (7 Milk Street)
2:00 PM: The 12th Annual Nantucket Nutcracker
Nantucket High School Auditorium (10 Surfside Road)
*Ed. Note: Also at 5:00 PM. A shorter, family-friendly production by the Nantucket Dance Theater. A sweet way to end the weekend.
5:00 PM: A Christmas Story: The Play
Theatre Workshop of Nantucket (62 Centre Street)